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Notes -
I think the insurance case is more intuitive if you think about it slightly differently: what would the company have been worth if Thomas Connolly had exercised his option to buy his brother's shares? Does anyone dispute it would have been worth the $6.86M? The company got the life insurance payout regardless of whether it would eventually have to pay it to either brother's estate, right? So Thomas Connolly's position implies that if he bought the shares they would be worth the $5.8M but if the company bought the shares they were only worth $3M.
At the moment of Michael's death the company gained an asset with about $3M of value. Eventually the company had to pay that money to fulfill an obligation, but that fact was by no means certain.
At a very high level, the entire structure here -- life insurance to the company's benefit to de-facto benefit a specific shareholder -- seems like an end-run around inheritance taxes from just gifting the shares in the estate. Even if you just gave the shares from the estate to the company to retire, I assume it would get taxed.
I guess the limits of that are a bit more fuzzy: if this was a broadly-held public company that benefit to shareholders would be a bit less clear, although plausibly still true.
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